Ethanol → 2-[1-(4-Bromophenyl)cyclopropyl]acetic acid

HRID 919063Notes

Reaction equation

HRID 919063 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(CC#N)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[OH-:14].[K+].[CH3:16][CH2:17][OH:18]>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:16][C:17]([OH:14])=[O:18])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 665793142-[1-(4-Bromophenyl)cyclopropyl]acetonitrile

Product 1

HCID 665776222-[1-(4-Bromophenyl)cyclopropyl]acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

[1-(4-Bromo-phenyl)-cyclopropyl]-acetonitrile (from previous step) was dissolved in EtOH (50 mL) and H2O (6 mL). Potassium hydroxide (5.4 g, 96 mmol) was added and the reaction was heated to reflux overnight. After cooling the reaction was submitted to standard aqueous workup and purified on silica gel to yield the title compound.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux overnight
  3. temperatureAfter cooling the reaction
  4. custompurified on silica gel

Sources & evidence

ORD record
ord-cce7871f1e1447a19adb7dc5820bf3e6
Source dataset
uspto-grants-2016_03
Patent number
US09272990B2

Reaction notes

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